Hydrochloric Acid → HCID 54347228, compound

HRID 1449406Notes

Reaction equation

HRID 1449406 reaction equation
[C:1]([CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=O)=[CH:8][CH:7]=1)([OH:3])=[O:2].[C:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=1)(=[O:16])[CH3:15].[OH-].[Na+].C(C1(OCC(O)=O)C=CC(C(=O)C=CC2C=CC=CC=2)=CC1)(O)=O.[Na].[Na].[Na][Na].Cl>O.C(O)C>[C:21]([C:20]1[CH:24]=[CH:25][C:17]([C:14](=[O:16])[CH:15]=[CH:10][C:9]2[CH:12]=[CH:13][C:6]([O:5][CH2:4][C:1]([OH:3])=[O:2])=[CH:7][CH:8]=2)=[CH:18][CH:19]=1)([OH:23])=[O:22]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 114704-Acetylbenzoic AcidHCID 14798Sodium HydroxideHCID 89177Acetic acid, 2-(4-formylphenoxy)-HCID 141233DisodiumHCID 70591733HCID 70591733, compound

Product 1

HCID 54347228HCID 54347228, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9.0 g. 4-Carboxymethoxy-benzaldehyde (see Example 5) and 8.2 g. 4-acetylbenzoic acid were dissolved in 50 ml. 10% aqueous sodium hydroxide solution and the solution stirred at ambient temperature for 2.25 hours. 150 ml. Ethanol were added and the solid precipitate obtained was filtered off, washed with ethanol and dried to give 16.9 g. disodium 4'-carboxy-4'-carboxymethoxy chalcone. This disodium salt was converted into the acid by dissolving in water, acidifying the solution with concentrated hydrochloric acid, filtering off the solid obtained, washing with water and drying, the yield being 15.1 g. Thin layer chromatography showed the presence of about 7% of polar impurities, most of which were removed by refluxing the solid with methanol, filtering and drying the undissolved solid, the yield being 11.9 g. Thin layer chromatography then showed the product to be about 98% pure. The solid was dissolved in dimethyl formamide and the solution was filtered and evaporated to a small volume. 200 ml. Methanol was added and the solid precipitate obtained was filtered off, washed with methanol and dried to give 8.0 g. of product, thin layer chromatography of which showed it to be more than 99% pure. The 4'-carboxy-4-carboxymethoxy-chalcone thus obtained had a melting point of 312°-314° C.

Workup

  1. customthe solid precipitate obtained
  2. filtrationwas filtered off
  3. washwashed with ethanol
  4. customdried
  5. customto give 16.9 g
  6. filtrationfiltering off the solid
  7. customobtained
  8. washwashing with water
  9. customdrying
  10. custommost of which were removed
  11. temperatureby refluxing the solid with methanol
  12. filtrationfiltering
  13. customdrying the undissolved solid
  14. dissolutionThe solid was dissolved in dimethyl formamide
  15. filtrationthe solution was filtered
  16. customevaporated to a small volume
  17. additionMethanol was added
  18. customthe solid precipitate obtained
  19. filtrationwas filtered off
  20. washwashed with methanol
  21. customdried
  22. customto give 8.0 g

Sources & evidence

ORD record
ord-4cf99f48a0134ad998005fa0c1cbea35
Source dataset
uspto-grants-1980_02
Patent number
US04190671

Reaction notes

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